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Recent Advances in the Chemistry of Oripavine and Its Derivatives

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DOI: 10.4236/abb.2014.58084    4,289 Downloads   5,406 Views   Citations
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ABSTRACT

Oripavine is the major alkaloid of Papaver orientale. It is an important intermediate in the biosynthesis of morphine alkaloids. Recently, new Papaver somniferum strains have been developed which accumulate thebaine and oripavine, but not morphine and codeine. Therefore, the chemistry of oripavine has been studied intensively to synthesize opioid pharmaceuticals such as oxymorphone, naloxone and buprenorphine.

Conflicts of Interest

The authors declare no conflicts of interest.

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Hosztafi, S. (2014) Recent Advances in the Chemistry of Oripavine and Its Derivatives. Advances in Bioscience and Biotechnology, 5, 704-717. doi: 10.4236/abb.2014.58084.

References

[1] Konowalowa, R., Yunosoff, S. and Orechoff, A. (1935) Uber Alkaloide der Papaver-Artem. I. Mitt.: Alkaloide von Papaver armeniacum und Papaver orientale. Berichte der Deutschen Chemischen Gesellschaft, 68, 2158-2163.
http://dx.doi.org/10.1002/cber.19350681135
[2] Shafiee, A., Lalezari, I., Nasseri-Nouri, P. and Asgharian, R. (1975) Alkaloids of Papaver orientale and Papaver pseudoorientale. Journal of Pharmaceutical Sciences, 64, 1570-1572.
http://dx.doi.org/10.1002/jps.2600640937
[3] Shafiee, A., Lalezari, I., Assadi, F. and Khalafi F. (1977) Alkaloids of Papaver orientale L. Journal of Pharmaceutical Sciences, 66, 1050-1052.
http://dx.doi.org/10.1002/jps.2600660742
[4] Delenk-Heydenreich, K. and Pfeifer, S. (1969) Uber Alkaloide der Gattung Papaver. Part 32. Papaver orientale. Pharmazie, 24, 635-645.
[5] Vincent, P.G., Bare, C.E. and Gentner, W.A. (1976) Rapid Semi-Quantitative Spot Test for Determination of Thebaine and Differentation of Papaver bracteatum from P. orientale and P. pseudo-orientale. Lloydia, 39, 76-78.
[6] Phillipson, J.D., Scutt, A., Baytop, A., Ozhatay, N. and Sariyar, G. (1981) Alkaloids from Turkish samples of Papaver orientale and P. pseudo-orientale. Planta Medica, 43, 261-271.
http://dx.doi.org/10.1055/s-2007-971507
[7] Slavik, J. and Slavikova, L. (1991) Polar Alkaloids from Papaver orientale L. Collection of Czechoslovak Chemical Communications, 56, 1534-1538.
http://dx.doi.org/10.1135/cccc19911534
[8] Sariyar, G. (1982) Alkaloids from Papaver cylindricum. Planta Medica, 46, 175-178.
http://dx.doi.org/10.1055/s-2007-971208
[9] Slavik, J. and Slavikova, L. (1994) Alkaloids from Papaver pinnatifidum Moris. Collection of Czechoslovak Chemical Communications, 59, 1879-1783.
http://dx.doi.org/10.1135/cccc19941879
[10] Bohm, H. (1981) Papaver bracteatum Lindl.—Results and Problems of the Research on a Potential Medicinal Plant. Pharmazie, 36, 660-667.
[11] Slavik, J. and Slavikova, L. (1985) Alkaloids from Papaver bracteatum Lindl. Collection of Czechoslovak Chemical Communications, 50, 1216-1226.
http://dx.doi.org/10.1135/cccc19851216
[12] Hodges, C.C., Horn, J.S. and Rapoport, H. (1977) Morphinan Alkaloids in Papaver bracteatum. Biosynthesis and Fate. Phytochemistry, 16, 1939-1942.
http://dx.doi.org/10.1016/0031-9422(77)80100-3
[13] Sariyar, G., Gulyeze, H.B. and Gozler, B. (1992) Salutaridine N-Oxide from the Capsules of Papaver bracteatum. Planta Medica, 58, 368-369.
http://dx.doi.org/10.1055/s-2006-961487
[14] Milo, J., Levy, A., Palevitch, D. and Ladizinsky, G. (1988) High Performance Liquid Chromatographic Analysis of the Alkaloid Spectrum in the Roots and Capsules of the Species and Hybrids of Papaver section Oxytona. Journal of Chromatography, 452, 563-570.
http://dx.doi.org/10.1016/S0021-9673(01)81480-1
[15] Nielsen, B., Roe, J. and Brochmann-Hanssen, E. (1983) Oripavine: A New Opium Alkaloid. Planta Medica, 48, 205-206.
http://dx.doi.org/10.1055/s-2007-969921
[16] Prajapati, S., Bajpai, S., Singh, D., Luthra, R., Gupta, M.M. and Kumar, S. (2002) Alkaloid Profiles of the Indian Land Races of the Opium Poppy Papaver somniferum L. Genetic Resources and Crop Evolution, 49, 183-188.
http://dx.doi.org/10.1023/A:1014763412736
[17] Stermitz, F.R. and Rapoport, H. (1961) The Biosynthesis of Opium Alkaloids. Alkaloid Interconversions in Papaver somniferum and Papaver orientale. Journal of the American Chemical Society, 83, 4045-4050.
http://dx.doi.org/10.1021/ja01480a022
[18] Brochmann-Hanssen, E. and Cheng, C. Y. (1982) Biosynthesis of Hydrophenanthrene Alkaloids in Papaver orientale. Journal of Natural Products, 45, 434-436.
http://dx.doi.org/10.1021/np50022a012
[19] Novak, B.H., Hudlicky, T., Reed, J.W., Mulzer, J. and Tauner, D. (2010) Morphine Synthesis and Biosynthesis—An update. Current Organic Chemistry, 4, 343-362.
http://dx.doi.org/10.2174/1385272003376292
[20] Ziegler, J., Facchini, P.J., Geissler, R., Schmidt, J., Ammer, C., Kramell, R., Voigtlander, S., Gesell, A., Pienkny, S. and Brandt, W. (2009) Evolution of Morphine Biosynthesis in Opium Poppy. Phytochemistry, 70, 1696-1707.
http://dx.doi.org/10.1016/j.phytochem.2009.07.006
[21] Hagel, J.M. and Facchini, P.J. (2013) Benzylisoquinoline Alkaloid Metabolism: A Century of Discovery and a Brave New World. Plant and Cell Physiology, 54, 647-672.
http://dx.doi.org/10.1093/pcp/pct020
[22] Horn, J.S., Paul, A.G. and Rapoport, H. (1978) Biosynthetic Conversion of Thebaine to Codeinone. Mechanism of Ketone Formation from Enol Ether in Vivo. Journal of the American Chemical Society, 100, 1895-1898.
http://dx.doi.org/10.1021/ja00474a041
[23] Hagel, J.M. and Facchini, P.J. (2010) Dioxygenases Catalyze the O-Demethylation Steps of Morphine Biosynthesis in Opium Poppy. Nature Chemical Biology, 6, 273-275.
http://dx.doi.org/10.1021/ja00474a041
[24] Brochmann-Hanssen, E. (1984) A Second Pathway for the Terminal Steps in the Biosynthesis of Morphine. Planta Medica, 50, 343-345.
http://dx.doi.org/10.1055/s-2007-969727
[25] Boettcher, C., Fellermeier, M., Boettcher, C., Drager, B. and Zenk, M.H. (2005) How Human Neuroblastoma Cells Make Morphine. Proceedings of the National Academy of Sciences of the United States of America, 102, 8495-8500.
http://dx.doi.org/10.1073/pnas.0503244102
[26] Grobe, N., Lamshoft, M., Orth, R.G., Drager, B., Kutchan, T.M., Zenk, M.H. and Spiteller, M. (2010) Urinary Excretion of Morphine and Biosynthetic Precursors in Mice. Proceedings of the National Academy of Sciences of the United States of America, 107, 8147-8152.
http://dx.doi.org/10.1073/pnas.1003423107
[27] Millgate, A.G., Pogson, B.J., Wilson, I.W., Kutchan, T.M., Zenk, M.H., Gerlach, W.L., Fist, A.J. and Larkin, P.J. (2004) Morphine-Pathway Block in Top1 Poppies. Nature, 431, 413-414.
http://dx.doi.org/10.1038/431413a
[28] Fist, A.J., Byrne, C.J. and Gerlach, W.L. (2011) Production of Thebaine and Oripavine. US Patent 8 067 213 B2..
[29] Gomez-Serranillos, M.P., Palomino, O.M., Carretero, E. and Villar, A. (1998) Analytical Study and Analgesic Activity of Oripavine from Papaver somniferum L. Phytotherapy Research, 12, 346-349.
http://dx.doi.org/10.1002/(SICI)1099-1573(199808)12:5<346::AID-PTR307>3.0.CO;2-A
[30] Singh, D.V., Prajapati, S., Bajpai, S., Verma, R.K., Gupta, M.M. and Kumar, S. (2000) Simultaneous Determination of Important Alkaloids in Papaver somniferum Using Reversed Phase High Performance Liquid Chromatography. Journal of Liquid Chromatography Related Technologies, 23, 1757-1764.
http://dx.doi.org/10.1081/JLC-100100450
[31] Yoshimatsu, K., Kiuchi, F., Shimomura, K. and Makino, Y. (2005) A Rapid and Reliable Solid-Phase Extraction Method for High-Performance Liquid Chromatographic Analysis of Opium Alkaloids from Papaver Plants. Chemical and Pharmaceutical Bulletin, 53, 1446-1450.
http://dx.doi.org/10.1248/cpb.53.1446
[32] Lenehan, C.F., Barnett, N.W., Lewis, S.W. and Essery, K.M. (2004) Preliminary Evaluation of Dual Acidic Potassium Permanganate and Tris(2,2'-bipyridyl)-ruthenium(II) Chemiluminescence Detection for the HPLC Determination of Papaver somniferum Alkaloids. Australian Journal of Chemistry, 57, 1001-1004.
http://dx.doi.org/10.1071/CH04084
[33] Costin, J.W., Lewis, S.W., Purcell, S.D., Waddell, L.R., Francis, P.S. and Barnett, N.W. (2007) Rapid Determination of Papaver somniferum Alkaloids Using Monolithic Column High-Performance Liquid Chromatography with Chemiluminescence Detection. Analytica Chimica Acta, 597, 19-23.
http://dx.doi.org/10.1016/j.aca.2007.06.044
[34] Hindson, B.J., Francis, P.S., Purcell, S.D. and Barnett, N.W. (2007) Detemination of Opiate Alkaloids in Process Liquors Using Capillary Electrophoresis. Journal of Pharmaceutical and Biomedical Analysis, 43, 1164-1168.
http://dx.doi.org/10.1016/j.jpba.2006.09.040
[35] Reid, R.G., Durham, D.G., Boyle, S.P., Low, N.S. and Wangboonskul, J. (2007) Differentiation of Opium and Poppy Straw Using Capillary Electrophoresis and Pattern Recognition Techniques. Analytica Chimica Acta, 605, 20-27.
http://dx.doi.org/10.1016/j.aca.2007.10.023
[36] Barnett, N.W., Hindson, B.J. and Lewis, S.W. (2000) Determination of Morphine, Oripavine and Pseudomorphine Using Capillary Electrophoresis with Acidic Potassium Permanganate Chemiluminescence Detection. Analyst, 125, 91-95.
http://dx.doi.org/10.1039/a906327g
[37] Odell, L.R., Skopec, J. and McCluskey, A. (2008) Isolation and Identification of Unique Marker Compounds from the Tasmanian Poppy Papaver somniferum N. Implications for the Identification of Illicit Heroin of Tasmanian Origin. Forensic Science International, 175, 202-208.
http://dx.doi.org/10.1016/j.forsciint.2007.07.002
[38] El-Haj, B.M., Ali, H.S. and Hamoudi, N.M. (2011) Oripavine as a New Marker of Opiate Product Use. Forensic Toxicology, 29, 152-158.
http://dx.doi.org/10.1007/s11419-011-0117-2
[39] Seki, I. (1970) Studies on the Morphine Alkaloids and Its Related Compounds. XVII. On-Step Preparations of Enol Ether and Pyrrolidinyl Dienamine of Normorphinone Derivatives. Chemical & Pharmaceutical Bulletin, 18, 671-676.
http://dx.doi.org/10.1248/cpb.18.671
[40] Coop, A. and Rice, K.C. (1998) A Novel Synthesis of Thebaine from Codeine. Heterocycles, 49, 43-47.
http://dx.doi.org/10.3987/COM-98-S8
[41] Rapoport, H., Reist, H.N. and Lovell, C.H. (1956) Codeinone Dimethyl Ketal and Its Conversion to Thebaine. Journal of the American Chemical Society, 78, 5128.
http://dx.doi.org/10.1021/ja01600a086
[42] Rapoport, H., Lovell, C.H., Reist, H.R. and Warren, M.E. (1967) The Synthesis of Thebaine and Northebaine from Codeinone Dimethyl Ketal. Journal of the American Chemical Society, 89, 1942-1947.
http://dx.doi.org/10.1021/ja00984a032
[43] Bartels-Keith, J.R. and Hills, D.W. (1967) Syntheses Related to Northebaine. Part II. Derivatives of Nororipavine and 8,14-Dihydronororipavine. Journal of the Chemical Society C, 434-440.
[44] Singer, R.D. and Scammells, P.J. (2001) Alternative Methods for the MnO2 Oxidation of Codeine Methyl Ether to Thebaine Utilizing Ionic Liquid. Tetrahedron Letters, 42, 6831-6833.
[45] Barber, R.B. and Rapoport, H. (1975) Synthesis of Thebaine and Oripavine from Codeine and Morphine. Journal of Medicinal Chemistry, 18, 1074-1077.
http://dx.doi.org/10.1021/jm00245a006
[46] Klein, P., Nelson, W.L., Yao, Y.H. and Simon, E.J. (1990) Electrophilic α-methylene-γ-lactone and Isothiocyanate Opioid Ligands Related to Etorphine. Journal of Medicinal Chemistry, 33, 2286-2296.
http://dx.doi.org/10.1021/jm00170a038
[47] Coop, A., Lewis, J.W. and Rice, K.C. (1996) Direct and Simple O-Demethylation of Thebaine to Oripavine. Journal of Organic Chemistry, 61, 6774.
[48] Coop, A., Janetka, J.W., Lewis, J.W. and Rice, K.C. (1998) L-Selectride as a General Reagent for the O-Demethylation and N-Decarbomethoxylation of Opium Alkaloids and Derivatives. Journal of Organic Chemistry, 63, 4392-4396.
http://dx.doi.org/10.1021/jo9801972
[49] Sipos, A., Berenyi, S. and Antus, S. (2009) First Synthesis and Utilization of Oripavidine—A Concise and Efficient Route to Important Morphinans and Apomorphines. Helvetica Chimica Acta, 92, 1359-1365.
http://dx.doi.org/10.1002/hlca.200800438
[50] McCamley, K., Ripper, J.A., Singer, R.D. and Scammells, P.J. (2003) Efficient N-Demethylation of Opiate Alkaloids Using a Modified Nonclassical Polonovski Reaction. Journal of Organic Chemistry, 68, 9847-9850.
http://dx.doi.org/10.1021/jo035243z
[51] Dong, Z.M. and Scammells, P.J. (2007) New Methodology for the N-Demethylation of Opiate Alkaloids. Journal of Organic Chemistry, 72, 9881-9885.
http://dx.doi.org/10.1021/jo071171q
[52] Kok, G.B. and Scammells, P.J. (2010) N-Demethylation of N-methyl Alkaloids with Ferrocene. Bioorganic & Medicinal Chemistry Letters, 20, 4499-4502.
http://dx.doi.org/10.1016/j.bmcl.2010.06.031
[53] Kok, G.B., Pye, C.C., Singer, R.D. and Scammells, P.J. (2010) Two-Step Iron(0)-Mediated N-Demethylation of N-Methyl Alkaloids. Journal of Organic Chemistry, 75, 4806-4811.
http://dx.doi.org/10.1021/jo1008492
[54] Kok, G.B. and Scammells, P.J. (2011) Further Investigations into the N-Demethylations of Oripavine Using Iron and Stainless Steel. Organic & Biomolecular Chemistry, 9, 1008-1011.
http://dx.doi.org/10.1039/c0ob01021a
[55] Kok, G.B. and Scammells, P.J. (2012) Improved Synthesis of 14-Hydroxy Opioid Pharmaceuticals and Intermediates. RSC Advances, 2, 11318-11325.
http://dx.doi.org/10.1039/c2ra21693k
[56] Machara, A., Cox, D.P. and Hudlicky, T. (2011) Synthesis of Nalbuphine from Oripavine via N-Demethylation of N-Cyclobutylmethyl Oripavine. Heterocycles, 84, 615-623.
[57] Werner, L., Machara, A., Adams, D.R., Cox, D.P. and Hudlicky, T. (2011) Synthesis of Buprenorphine from Oripavine via N-Demethylation of Oripavine Quaternary Salts. Journal of Organic Chemistry, 76, 4628-4634.
http://dx.doi.org/10.1021/jo200567n
[58] Machara, A., Werner, L., Endoma-Arias, M.A., Cox, D.P. and Hudlicky, T. (2012) Improved Synthesis of Buprenorphine from Thebaine and/or Oripavine via Palladium-Catalyzed N-Demethylation/Acylation and/or Concomitant O-Demethylation. Advanced Synthesis & Catalysis, 354, 613-626.
http://dx.doi.org/10.1002/adsc.201100807
[59] Mannino, A., Hoefgin, E.R., Hill, L.P. and Buehler, H.J. (2008) Use of Oripavine as a Starting Material for Buprenorphine. United States Patent, US 2008/0312441 A1.
[60] Wang, P.X., Jiang, T., Cantrell, G.L. and Berberich, D.W. (2012) Preparation of Oxymorphone from Oripavine. United States Patent, US 8,217,175 B2.
[61] Wang, P.X., Jiang, T., Cantrell, G.L. and Berberich, D.W. (2012) Opiate Reduction Utilizing Catalytic Hydrogen Transfer Reaction. United States Patent, US 8,309,727 B2.
[62] Huang, B.S. (2012) Process for Preparing Oxymorphone. United States Patent, US 8,134,002 B2.
[63] Huang, B.S. (2013) Process for Preparing Oxymorphone. United States Patent, US 8,357,802 B2.

  
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